[(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-(ethylsulfanyl)oxan-2-yl]methyl acetate

• ChemBase ID: 168756
• Molecular Formular: C16H24O9S
• Molecular Mass: 392.42136
• Monoisotopic Mass: 392.11410335
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)C)SCC)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CCS[C@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C16H24O9S/c1-6-26-16-15(24-11(5)20)14(23-10(4)19)13(22-9(3)18)12(25-16)7-21-8(2)17/h12-16H,6-7H2,1-5H3/t12-,13-,14+,15+,16-/m1/s1
• InChIKey: YPNFVZQPWZMHIF-RBGFHDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-(ethylsulfanyl)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-(ethylsulfanyl)oxan-2-yl]methyl acetate
• Synonyms: Ethyl 1-Thio-α-D-mannopyranoside Tetraacetate; Ethyl 2,3,4,6-Tetra-O-acetyl-1-thio-α-D-mannopyranoside; Ethyl 2,3,4,6-Tetra-O-acetyl-α-D-thiomannopyranoside(contains up to 20% beta isomer)

Database IDs

• CAS Number: 79389-52-9
• PubChem SID: 162262888
• PubChem CID: 10992845

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.43911013
• LogD (pH = 7.4): 0.43911013
• Log P: 0.43911013
• Molar Refractivity: 88.1986 cm^3
• Polarizability: 36.55362 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 103-105°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E926250

A useful reagent for the preparation of mannosides.

REFERENCES

• Peter, T., et al.: Liebigs Ann. Chem., 237 (1991)